Problem

The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) give...

The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) givestwo products:

(a) Give a mechanism for this reaction, showing how the two products arise as a consequence of the resonance-stabilized intermediate.

(b) The bromination of cyclohexene using NBS gives only one major product, as shown onpage 227. Explain why there is no second product from an allylic shift.

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Solutions For Problems in Chapter 6

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